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Chicago, IL could be the perfect boating playground for you

Discover Chicago by private yacht charter with Sailo. Enjoy a whole other side of Illinois on a boat rental with captain, or skipper yourself if you prefer. Whatever your boating needs, you’ll find the perfect charter boat for your sailing trip, party or special event. Enjoy sunset cruises, watersports or fishing trips, or a day out with family and friends for a memorable experience on a Sailo boat.

Our premium inventory of Chicago, IL private sailboat charters

Chicago, IL is a well-known boating destination in the US, perfect for a memorable experience on a Sailo boat. The sailboat rentals are popular for both locals and tourists and a great choice if you want to spend some quality time with your family or friends. 11 charters are currently available with or without captain, lined up in the Chicago’s marinas, waiting for their guests. Rent a private sailboat in Chicago with Sailo: it’s easy, quick, secured and the best choice for a fun experience in the waters of Illinois.

Learn how to find the perfect yacht for you

Sailo has the most advanced filters to help you find the perfect boat rental for an amazing experience on the water in Chicago, IL. Start your search by choosing your start trip date, duration and number of guests. For a great day trip with your family or friends, you have the option to select 2, 4 hours or full day rentals. Depending on your preferences and budget, you may narrow your results by boat type and price range. The 'crew' filter allows you to check the boat rentals with the captain included in the price, skipper optional (paid as extra) or bareboats that you’ll captain yourself (boating resume required). Once you have laid your eyes on a boat you like in Illinois, click on it to read the description, reviews and see more pics. We also recommend using our direct 'Message Owner' feature that allows you to start a conversation with the boat representative to ask away everything you want to know before you submit a booking request.

How much is it to charter a Chicago, IL yacht for a day?

Whether you are looking to rent a yacht for a city sightseeing tour, a romantic sunset cruise or an active day on the water with your family or friends, we're confident you’ll find the best one for you on Sailo. The average starting price to charter a yacht in Chicago is $1100. You can however find excellent affordable rentals from $250 and also elegant yacht charters that can go up to $6500 (service fee and mandatory extras not included).

Essential safety tips for recreational boating

Whether you’re renting a boat with captain or you choose a bareboat, always keep in mind this basic safety guidelines:
  • if you rent a captained charter, always pay close attention to your captain
  • walk slowly and never run onboard as you can easily slip and fall overboard
  • be mindful of stairs and hatches (never step on them)
  • if you go swimming, floating or paddling, stay away from other boats even if they are anchored or moored
  • pay attention to the other group members and make sure that everybody is accounted for at all times

Sustainable yachting tips

If you’re looking to explore our beautiful planet, a yacht charter is a great place to start. Explore coral reefs with your snorkel, discover hidden bays and islands and generally enjoy the view of nature. Remember, that sailing motto: 'Take only photos, leave only wake' (OK, so we paraphrased). To be a responsible sailor, remember:
  • Don’t disturb coral or sealife
  • Take your trash home (and don’t throw anything in the sea)
  • Respect the locals and their customs wherever you go
Read more about responsible boating.